A constricting fit

The panties glided up his legs, but when they reached his hips, two things became apparent:

1. They needed to ride up his ass to fit properly
2. These were clearly not meant to hold a dick and balls.

As he pulled them up in his usual way, his balls slipped inside, but his dick was another story. If he left it flopping over the waistband, the rest of it hugged his ass, but wasn't uncomfortable. It just left him exposed. He tried to tuck his sizable cock inside, but that made it slip down in the back, and exposed the top of his ass, unless he tugged on the back, giving himself a partial wedgie. It also made his dick liable to poke out of one of the leg holes. No matter what he did, he was either going to expose his dick or be uncomfortable.

"Hey, you ok over there?" His roomate asked, only seeing the show from behind.

Avery blushed, but tucked his dick into the underwear and turned around. Sofia burst out laughing as she saw how ridiculous he looked.

"HAHAHAHAaaaah dude! You can't be contained!" She joked, pointing at his crotch.

"Could I ask for a bigger size?" Avery blushed, but knew there was nothing to be done right now.

"Sure, but it will still take a while to deliver it to you. Just stick with it for now. You said you wanted to wear the shorts?" She tried to distrct him.

Avery nodded and picked up the black spandex shorts. These were clearly meant to be worn while working out or running. The school's logo was on the left leg and the hem and sides of the shorts were accented by the school's color, Magenta. Pulling them up his legs, he was thankful his hips fit, but these were clearly made for girls who don't mind showing off their thighs and curves. It hugged every inch of him from the upper thighs to his waist. They covered about the same as his boxer briefs, but he also realized, as with the panties, the shorts didn't have much room for his dangly bits. His crotch felt like it was suffocating, but the shorts stretched so it wasn't like he was bound to burst out at any time. He turned around to get an appraisal from Sofia.

"Well, despite the VPL, not bad." She smiled.

"VPL?" Avery asked, unsure what that meant.

"Visible Panty Lines, though in your case it can also mean 'Visible Penis Lines'." She joked.

Avery decided to put on the dress shirt that was meant to be worn at all times. He was thankfully able to button it all the way, even though it did cinch in at the waist to give girls more of an hourglass figure. It was a bit snug, but fit nicely. He was at least thankful he didn't have to tuck it in since it sat at the waistband of the shorts. So, it didn't have the unattractive shirt tails that he was used to.

"You look ridiculous! No girl ever wears the gym shorts and blouse together. We will have to see how you fare when the professors see you in that. Though you may need to pack the skirt just in case someone wants you to be formal and wear the full uniform." Sofia said.

Avery blushed as she handed him the skirt. He didn't want to have to make a full feminization transformation. However, he did understand that professors all have different rules and ways of conducting their class, so he gulped and pushed the shorts down. As he did, he didn't think to turn around since Sofia already saw him in the panties, but the shorts were so tight, it pulled the underwear down with it, exposing his naked crotch to her once again!

CLICK
FLASH

Avery's eyes shot open as he looked up to see Sofia holding her phone, having just taken a picture of him wearing a women's blouse and mostly naked from the waist down. Avery blushed and covered his crotch with the skirt.

"Come on! Delete that!" Avery whined, reaching for her phone.

"Nuh uh! I'm sure the ladies around campus will love to see what you're packing into those shorts." Sofia smirked, hovering her finger over the screen.

Avery couldn't see if she was about to send it or not, but he lunged for the phone again, dropping the skirt, and unknowingly stepping out of the shorts and panties. Avery chased Sofia around the room, before she ran outside into the hallway.

Avery was about to run after her, but realized his exposed state. He knew he had to get dressed quickly,, but wasn't sure he should go for the skirt on it's own or pull on his panties and shorts. He wasn't sure he could trust her with that picture, and the longer he took meant the farther she may run away, r possibly show it to as many people she could.